Potassium Phosphate, Tribasic → 8-Fluoro-2-(4-methyl-pyridin-3-yl)-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one

Participants

Role	Name	HCID	Charge
Reactant	Potassium Phosphate, Tribasic	HCID 62657	—
Reactant	trans-N,N'-dimethyl-1,2-cyclohexanediamine	HCID 2733821	—
Reactant	3-Iodo-4-methylpyridine	HCID 14423513	—
Reactant	8-fluoro-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one	HCID 66802009	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	8-Fluoro-2-(4-methyl-pyridin-3-yl)-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one	HCID 56943048	4.8%

Reaction Conditions

Temperature	110 °C

Reaction Steps

8-Fluoro-7-trifluoromethyl-3,4-dihydro-2H-isoquinolin-1-one (I-47d: 150 mg, 0.643 mmol) was reacted with 3-iodo-4-methyl-pyridine (140.98 mg, 0.643 mmol), K3PO4 (346.76 mg, 1.607 mmol), trans-N,N′-dimethyl-cyclohexane-1, 2-diamine (0.03 mL, 0.192 mmol), CuI (12.24 mg, 0.0643 mmol) and 1,4-dioxane (10 mL). The resulting mixture was refluxed for 16 hours at 110° C. to afford the crude product. Purification by column chromatography on silica gel (40% ethylacetate in hexane) followed by preparative HPLC afforded 10 mg of the product (4.8% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946260B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-8b5bf56f300743459b6580267eb7427d
Source note	uspto-grants-2015_02